But once you declare to be running a trade or business - then 1099s do come with the territory.If you really want to avoid 1099s and decide to claim to NOT be running a trade or business - be prepared to lose your business overhead deductions upon an IRS audit.

You can make great profits flipping houses, but you can also lose a ton if you don't do it right.That said, I encourage you to be in touch with an investor friendly agent in Indy.

In 2017 we started our journey with long-term buy-and-hold investment properties in the Memphis, TN area after selling a property that we were losing money on every month in NOVA that we purchased as a primary residence in Jan 2007 (talk about all-time bad timing) and then had to move with the Navy in 2009 (2nd all-time worst timing).

@Kyle LumanKeep in mind everyone's situation is different and while one investor in the short term is wanting less cash flow for tax reasons (presumably) your situation it might not make sense to break even or lose money.

Options are very good, just need to avoid sharp dips because I am wagering about 1k at a time and any bad luck and I lose the entire 1k.

If you own a business that you have no understanding of, how in the world do you expect to not lose? 

In that case, the only way you could lose money is if your property lose value and you have to sell at a capital loss.

A the town and amenities expands towards the beach, there is a real risk that properties on town side will relatively lose value in my opinion.

Without membership association I lose access to the official forms and the software.

Meanwhile during the eviction period, we finalized our architectural plans and started the permitting process in the county so we didn't lose much time.